Process for the dyeing of textile material made from mixtures of polyester and cellulosic fibers

ABSTRACT

PROCESS FOR THE DYEING OF TEXTILE MATERIAL CONSISTING OF MIXTURES OF POLYESTER AND CELLULOSE FIBERS, WHEREIN SAID TEXTILE MATERIAL IMPREGINATED WITH AN ALKALINE SOLUTION CONTAINING A SUBSTANTIALLY COUPLING COMPONENT, AS WELL AS A WETTING OR DISPERSING AGENT, DRIED, SUBSEQUENTLY TREATED WITH AN ACID AQUEOUS SOLUTION CONTAINING A DIAZOTIZED AROMATIC AMINE AND A COMPOUND HAVING AN ACIDIC REACTION, FRIED, IMPREGNATED WITH AT LEAST ONE DISPERSE DYESTUFF AND THEN SUBJECTED TO A HEAT-TREATMENT.

United States Patent U.S. Cl. 821 C 6 Claims ABSTRACT OF THE DISCLOSUREProcess for the dyeing of textile material consisting of mixtures ofpolyester and cellulosic fibers, wherein said textile material isimpregnated with an alkaline solution containing a substantive couplingcomponent, as well as a wetting or dispersing agent, dried, subsequentlytreated with an acid aqueous solution containing a diazotized aromaticamine and a compound having an acidic reaction, dried, impregnated withat least one disperse dyestuff and then subjected to a heat-treatment.

It is known that textile material made from mixtures of polyester andcellulosic fibers can be dyed fast shades by using disperse dyestuffsand water-insoluble azo dyestuffs, the latter being'produced on thefiber. The procedure is as follows: 'the polyester fiber portion of thegoods is first dyed with disperse dyestuifs, either at boilingtemperature in the presence of dyeing accelerators, or under theconditions of high-temperature dyeing, or according to the so-calledThermosol process; subsequently the water-insoluble azo dyestufr isproduced on the cellulosic fiber portion by impregnating the textileswith a coupling component and thereafter developing the dye with adiazotized aromatic amine.

In many cases, this process yields dyeings of useful quality. In othercases, especially with the production of blue, water-insoluble azodyestuffs on the cellulosic fiber portion of the mixed fabrics, dyeingsresult the fastness of which to rubbing does not comply with thepractical requirements.

The cause of the deficient fastness to rubbing may be seen in the factthat during development a certain portion of the water-insoluble azodyestuif is formed in the surface zone of the polyester fiber portionand is not removed during the following washing process. This dyestutfwhich sticks to the polyester fiber portion is rubbed off on abrasion ofthe dyed fabric by means of undyed material and renders the dyeingsubstantially useless.

This invention is based on the observation that the aforesaiddisadvantages in the dyeing of textile material made from mixtures ofpolyester and cellulosic fibers can be overcome by impregnating saidtextile material with alkaline solutions containing a coupling componentas well as wetting or dispersing agents, drying and subsequentlytreating the material with aqueous solutions of acidic agents whichcontain a diazotized aromatic amine and a compound having an acidicreaction, drying, impregnating with at least one disperse dyestutf andthen subjecting it to a heat-treatment.

The process of the invention is carried out as follows: the textilematerial, for example mixed fabrics made from polyester and cellulosicfibers, is impregnated with an alkaline solution containing a couplingcomponent, as well as wetting or dispersing agents, squeezed and thendried. Thereby, the alkali concentration of the impreg nation bathshould be kept at such a high level which ensures non-precipitation ofthe coupling component during impregnation. Subsequently, the textilematerial is impregnated with a solution containing compounds having anacidic reaction, a diazotized primary aromatic amine, as Well as, ifdesired or required, a dispersing agent. The concentration of thecompounds having an acidic reaction should be at a level which ensuresneutralization of the alkali applied to the textile material togetherwith the coupling component in the alkaline impregnation process, andthe material to be dyed should have a pH-value of from 4 to 7.Corresponding to the coupling capability of the diazotized aromaticamine used, the goods are subsequently treated in a neutral or alkalinecold or warm bath in order to complete coupling.

After dyestuff formation, the material is subjected to an alkalineafter-treatment in usual manner at boiling temperatures, rinsed anddried. Subsequently, it is impregnated with the aqueous suspension of atleast one disperse dyestuif, squeezed, dried and the textile material issubjected to a heat-treatment in the range of from about 170 to 220 C.This heat-treatment may be carried out by means of hot air or contactheat. In the process of the invention, remainders of the insoluble azodyestufi, which had not been washed out before, and the dispersedyestuff applied at last, migrate into the interior of the polyesterfiber during the heat treatment and are there fixed. Finally, thematerial is subjected to an alkaline after-treatment, rinsed and dried.

On this method, the azo dyestuif is obtained in full yield andclearness. The dyeingsobtained have a better fastness to rubbing thandyeings .with which first the disperse dyestutf was fixed separately byheat-treatment on the polyester fiber portion and the water-insolubleazo dyestutf was subsequently produced on the cellulosic fiber portionin known manner.

Examples of the textile material to be dyed are mixtures containingbetween 25% of polyester and of cellulosic fibers and 70% of polyesterand 30% of cellulosic fibers.

Suitable polyester fibers in the blend are fibers made from aromaticpolyesters, for example from terephthalic acid ordiphenyl-4,4'-dicarboxylic acid and alkane diols or1,4-cyclohexane-di-methanol, as well as those consisting of triacetylcellulose. The cellulosic fiber portion may be of natural or regeneratedorigin.

Examples of the coupling components to be used in the process of theinvention are especially aromatic ohydroxycarboxylic acid arylamides oracylacetic acid arylamides, 6-bromoor 6-alkoxy-2,3-hydroxynaphthoic acidarylamides or acetoacetic acid arylamides which have a low to mediumsubstantivity towards cellulosic fibers. When suitable impregnationequipment is used, for example one with a small-sized bath tank,coupling components having a high substantivity towards cellulosicfibers may also be used, for example the condensation products from2,3-hydroxynaphthoic acid and polynuclear, isocyclic and heterocyclicamines, for example aminonaphthalenes, aminocarbazoles oraminodiphenyleneoxides.

As diazotized primary aromatic amines monoor diamines may be used, forexample diazotized chloroanilines, dichloroanilines, chlorotoluidines,chloroanisidines, nitranilines, nitrotoluidenes, nitroanisidines,nitroxylidines, nitrophenetidines, cyanotoluidines, cyanoanisidines,aminobenzene sulfonic acid amides, aminobenzene carboxylic acid amides,aminophenyl-alkylsulfones, aminophenyl-arylsulfones oraminophenyl-aralkylsulfones, aminodiphenyl ethers,trifiuoromethylanilines, monoacylated phenylenediamines,aminoazobenzenes, as well as tetrazo- 4,4'-diamino-diphenyls.

3 Suitable wetting or dispersing agents in the alkaline impregnationbath are condensation products from highmolecular fatty acids andprotein degradation products, condensation products from high-molecularfatty acids 4 passed into water of the temperature of 60 C.,subsequently subjected to alkaline washing and dried. The material wasthen impregnated 'by means of an aqueous suspension of 40 g. of thedisperse dyestuif: aniline 1-(2',3'-

and aminoalkyl sulfonic acids, condensation products 5hydroxynaphthoylamino)-4-methoxybenzene per liter of from formaldehydeand naphthalene sulfonic acids, Monwater, squeezed in such a way thatthe liquor uptake opol brilliant oil as well as purifiedsulfite-cellulose amounted to 60% of the dry weight of the material,dried waste liquor. and passed through a fixing chamber or over hotrollers The compounds having an acidic reaction may be orin such a waythat the goods were heated for 30-60 secganic acids, for example aceticacid, formic acid, propionds to 1-80" C.-210 C. onic acid, glycolicacid, tartaric acid or citric acid, com- Finally, the fabric wasafter-treated, at boihng templex chromium salts of the acetic acid whichhave weakly perature, with a solution containing 2 g. of a 30% reacidicreaction or other salts having an acidic reaction, action product ofabout 10 mols of ethylene oxide with for example monosodium phosphate oraluminium 1 mol of nonylphenol, 2 ml. of a 25% solution of the sulf tsodium salt of nitrilotriacetic acid and 2 g. of sodium As dispersedyestuffs there may be used such dyestuffs carbonate per liter of waterand then rinsed hot and which are suitable for the Thermosol process onaccount cold- The after-treatment 0f the y fahl'lc might also o of theirthermal propertles, 1.e. dyestufis which are capabe calmed out at 60 95111 a bath Contalhlhg, ble of dyeing polyester fibers at temperatures inthe range Per hter of water 3 a mlxture of 63% Perchlom' of from 170 to220 C. and which do not soil the dyeii f g gig ing equipment on accountof high volatility. Suitable dis- 2 g fi g 'gi g perse dyestuffs of theazo and anthraquinone series are p g 0 described in colouplndex secondedition 1959 vol 1 of the SOdllllIl salt of mtrilo-triacetic acid. Anintense red 1659 1742 d S 1 1963 S dyeing having good fastnessproperties was obtained. 1 T h an d as 25 The following table listsfurther coupling components, We 1 as t e correspon mg addmons and amenments diazo components and disperse dyestuffs that may be used 1(September 23 P according to the process of the invention, as well asthe The Process of the lhvehtloh y t: earned out 6011- shades obtainabletherefrom on mixed fabrics containing tinuously or sem1-cont1nuously.67% of polyethylene terephthalate fibers and 33% of The followingexample illustrates the invention. cotton.

Coupling component Diazo component Disperse dyestufi Shade 1-(2',3-hydroxynaphthoylamino)-2-l-arnino-3-chlorobenzenel-amino4-phenylazonaphthalenephenol Orange.

methoxybenzene. 2,3-hydroxynaphthoylaminobenzene.l-amlno-2-nitro-4-ehlorobenzene..l-amino-4-nitrobenzener3-methy1-N,N-bis-B- Red.

hydroxyethylaniline. Do 1-amino-4-chloro-2-tnfiuorornethyl- Aniline1-2,3-(hydroxynaphthoylamino)-4- Yellowish benzene. methoxybenzene plus1-amino-4-nitrobenzene- 3- red.

methyl-N ,N-bis-B-hydroxyethylaniline. Do1-amino-2-methoxy-4-mtrobenzene 1-amino-2cyano-4-nitrobenzeneN,N-bls-(fl- Bluish red.-

acetoxyethyD-aniline. Do o-aminoazotoluene do Scarlet.1-(2,3-hydroxynaphthoylaznino)- l-amino-2-methyl-fi-chlorobenzene-1-amino-2-cyano-4-nitrobenzene- N-fl-eyanoethyl-N- Red.

Zagethoxybenzene. d B-carbomethoxyethylaniline. R d

0 0 O B l-acetoacetyl amino-2,5-dimethoxy-4-1-a1nino-2-methyl-4-ehlorobenzene-. 1-amino-3-nitrobenzene4-hydroxy-l-methylcarho- Yellow.

chlorobenzene. styryl.

Do l-amino-lchlorobenzene do Do. 4,4 -his-acetoacetylamino-3,3- do doDo.

dimethyl-diphenyl. 1-(2,3-l1ydroxynaphthoylamino)-Z-1-a1nino-2-methyl-5-chlorobenzene l-amino-2-cyano-4-nitrobenzene-N-B-cyanoethyl-N- Red.

methyl-4-chlorobenzene. I B-carbomethoxyethylaniline.2,8-hydroxynaphthoylaminobenzene.. 4-amino-4-methoxydrphenylamine-.1,5-dihydroxy-4,8-diamino-bromoanthraquinone Blue.

Do 4-amino-2,5-din1ethoxy-2,6- l-amino-2-bromo-4,6-dinitrobenzene-2-ethoxy-5- Navy blue.

dichloro-4-n1tro-1,l-azobenzene.acetylamino-N,N'bis-(fi-aeetoxyethyl)-an.iline pluslamino-3-nitrobenzene- 4-hydroxy-l-methylcarbostyryl plus1-amino-2-cyano-4-nitrobenzene N-B-cyanoethyl-N-fl-carbomethoxyethylaniline.1-(2,3-hydroxynaphthoylamino)-2, do 1-amino-2-bromo-4,G-dinitro-benzene2'ethoxy-5- Do.

4-dimethoxy-5-ch1orobenzene. acetylamino-NN-bis-(B-acetoxyethyl)-aniline plus 1-amino-3-nitro enzene-4-hydroxy-l-methylcarbostyryl plus l-amino-Z-cyano-4nitrobenzene- N-B-eyanoethyl-N-B-carbomethoxyethylaniline.2,3-hydroxynaphthoylaminobenzene. 1-ammo-4-benzoylammo-2,5-1,8-dihydroxy-4,5-diaminoanthraquinone Blue.

diethoxy-benzene.

EXAMPLE A mixed fabric .consisting of 67% of polyethylene terephthalatefibers and 33% of cotton was impregnated with a solution containing perliter of water 14 g. of 2,3- hydroxynaphthoylaminobenzene dissolved in14 ml. of 32.5% sodium hydroxide solution and water of the temperatureof 90 C., as well as 4 g. of a Wetting agent of the type of the oleicsulfonates. The fabric was then squeezed in such a way that the liquoruptake amounted to 60% of the dry weight of the material, dried andimpregnated wtih a solution containing per liter of water 7.6 g. ofdiazotized 1-amino-2-nitrobenzene, 20 ml. of acetic acid and 15 g. ofsodium acetate, and once more squeezed in such a way that the liquoruptake amounted to of the dry weight of the material. After an airpassage of about 60 seconds, the goods were What we claim is:

1. A process for the dyeing of textile material consisting of mixturesof polyester and cellulosic fibers, wherein said textile material isimpregnated with an alkaline solution containing a substantive couplingcomponent, as well as a wetting or dispersing agent, dried, subsequentlytreated with an acid aqueous solution containing a diazotized aromaticamine and a compound having an acidic reaction, dried, impregnated withat least one disperse dyestufi and then subjected to a heat-treatment.

2. A process as claimed in claim 1, wherein the coupling component is anaromatic or heterocyclic ohydroxycarboxylic acid arylamide or anacetoacetic acid arylamide.

3. A process as claimed in claim 1, wherein a dia zo OTHER REFERENCEScompound of the benzene, drphenyl or azobenzene series Fortess et a1Amen Dyestufi Report?r May 1963 pp is used. 402409.

A process as claimed in claim i a disperse Schmidlin, Preparation andDyeing of Synthetic Fibers, dyestufi anthmqmime 5 Publ. April 1963 byChapman & Hall Ltd pp 264274 5. A process as claimed in claim 1, whereinthe acid W J W Amer D estufl Re fDecembel: impregnation is carried outat a pH in the range of from 1964' pi g y p 6. A process as claimed inclaim 1, wherein the heat- DuPont Bulletin D438 March 1970 treatment iseffected at a. temperature within the range 10 I I of from to C. GEORGEF. LESMES, Primary Examiner References Cited UNITED STATES PATENTS 3 2646 3,416,873 12/1968 Fono et a1. 821 C 3,100,132 8/1963 Jenny et a1.8-39 T. J. HERBERT, IR., Assistant Examiner US. Cl. X.R.

